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Synthesis Of Trifluoromethyl-containing Quinoline And Isoquinoline Derivatives Via Tandem Reactions

Posted on:2015-10-13Degree:MasterType:Thesis
Country:ChinaCandidate:M L LiuFull Text:PDF
GTID:2181330431998541Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
As privileged fragments, the quinoline and isoquinoline cores are ubiquitoussubumits in many alkaloids with remarkable biologieal activities. Furthermore,Fluorine-containing heteroarenes are widely used as active ingredients of numerousmodern pharmaceuricals and agrochemicals. In particular, trifluoromethyl group candramatically modify the bioavailability and stability of target molecules because ofthe strong electron-withdrawing nature and large hydrophobic domain of CF3. Weenvisage the introduction of trifluoromethyl-quinoline and isoquinoline skeletoncompound to make it more bioactive. We designed and synthesised a number ofquinoline and isoquinoline derivatives containing trifluoromethyl group. The methodsfor construction of fluorochemicals are divided into two categories: one is directfluorination method, and the other is using fluorine-containing building-block. Thisthesis covered fluorine-containing building-block.We describe an efficient method for one-pot synthesis of trifluoromethylatepyrazolo [5,1-a] isoquinoline drivates via a tandem Lewis acid (AgOTf) orelectrophile (I2or ICl) promoted annulations and the following1,3-dipolarcycloaddition.We designed a new, rapid, and high-yielding synthetic approach to3,4-disubstituted2-trifluoromethylquinoline via Cu-catalyzed oxidative cyolization underextremely mild condition from o-alkynyl enamine.
Keywords/Search Tags:Trifluoromethyl building-block, quinoline, isoquinoline, o-alkynylbenzaldehyde hydrazone, tandem reaction, o-alkynyl enamine
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